Dimethylformamide dimethyl acetal → HCID 67260374, compound

HRID 2359024Notes

Reaction equation

HRID 2359024 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:16])[C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[CH2:9].CO[CH:19](OC)[N:20](C)[CH3:21]>CN(C)C=O.O>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:16])[C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[CH:9][N:20]([CH3:21])[CH3:19]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67389467HCID 67389467, compound

Product 1

HCID 67260374HCID 67260374, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-chlorothiophen-2-yl)-2-(pyridin-4-yl)prop-2-en-1-one (1 eq, 27 mmol) in anhydrous N,N-dimethylformamide (40 mL) was added N,N-dimethylformamide dimethyl acetal (4 eq, 108 mmol). The reaction mixture was stirred under reflux for 1.5 h. The mixture was diluted with water (600 mL) and extracted with dichloromethane (4×200 mL) and ethylacetate (4×200 mL). The combined extracts were washed with water, brine, dried over Na2SO4 and concentrated. The obtained residue was purified by column chromatography on silica gel (DCM:MeOH, 40:1 to 20:1) to afford intermediate 5.9 g of 1-(3-chlorothiophen-2-yl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one (74% yield).

Workup

  1. temperatureunder reflux for 1.5 h
  2. extractionextracted with dichloromethane (4×200 mL) and ethylacetate (4×200 mL)
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (DCM:MeOH, 40:1 to 20:1)

Sources & evidence

ORD record
ord-4912ed8b984a4046bfaf6d0c0a037ee8
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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